CA1182242A - Polyesters ioniques pour particules produits et elements electriquement photosensibles, et methodes de formation photoelectrophoretique d'images - Google Patents

Polyesters ioniques pour particules produits et elements electriquement photosensibles, et methodes de formation photoelectrophoretique d'images

Info

Publication number: CA1182242A
Authority: CA; Canada
Prior art keywords: bis; alkyl; alkylene; poly; ethyl
Prior art date: 1981-04-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000401503A

Other languages

English (en)

Inventor

Henry V. Isaacson

Michael T. Regan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

NexPress Solutions LLC

Original Assignee

Eastman Kodak Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-04-22

Filing date

1982-04-22

Publication date

1985-02-05

1982-04-22 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1985-02-05 Application granted granted Critical

1985-02-05 Publication of CA1182242A publication Critical patent/CA1182242A/fr

Status Expired legal-status Critical Current

Links

238000003384 imaging method Methods 0.000 title claims abstract description 71
239000000463 material Substances 0.000 title claims abstract description 58
239000011246 composite particle Substances 0.000 title claims abstract description 53
229920000728 polyester Polymers 0.000 title claims abstract description 52
150000002009 diols Chemical class 0.000 claims abstract description 26
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 15
150000001340 alkali metals Chemical class 0.000 claims abstract description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 11
150000004982 aromatic amines Chemical class 0.000 claims abstract description 7
150000001924 cycloalkanes Chemical class 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 43
239000002245 particle Substances 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 28
238000000034 method Methods 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 26
USSHTWOXWQEPPI-UHFFFAOYSA-N 6-sulfonylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound OC(=O)C1C=CC=CC1=S(=O)=O USSHTWOXWQEPPI-UHFFFAOYSA-N 0.000 claims description 24
239000003086 colorant Substances 0.000 claims description 22
230000005684 electric field Effects 0.000 claims description 21
125000000732 arylene group Chemical group 0.000 claims description 20
-1 phenylmethylene, diphenyl-methylene, phenylethylidene, cyclohexylidene Chemical group 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
229920000642 polymer Polymers 0.000 claims description 15
125000002993 cycloalkylene group Chemical group 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
230000005670 electromagnetic radiation Effects 0.000 claims description 9
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 8
239000002131 composite material Substances 0.000 claims description 7
125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
QFHMNFAUXJAINK-UHFFFAOYSA-N [1-(carbamoylamino)-2-methylpropyl]urea Chemical group NC(=O)NC(C(C)C)NC(N)=O QFHMNFAUXJAINK-UHFFFAOYSA-N 0.000 claims description 6
239000011230 binding agent Substances 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000006356 alkylene carbonyl group Chemical group 0.000 claims description 5
125000005529 alkyleneoxy group Chemical group 0.000 claims description 5
QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 claims description 5
230000000007 visual effect Effects 0.000 claims description 5
125000002877 alkyl aryl group Chemical group 0.000 claims description 4
FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 4
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
125000004956 cyclohexylene group Chemical group 0.000 claims 4
238000009740 moulding (composite fabrication) Methods 0.000 claims 2
125000005275 alkylenearyl group Chemical group 0.000 claims 1
239000010410 layer Substances 0.000 abstract description 65
239000000049 pigment Substances 0.000 description 29
239000007788 liquid Substances 0.000 description 28
230000005855 radiation Effects 0.000 description 19
239000006185 dispersion Substances 0.000 description 18
239000000306 component Substances 0.000 description 13
230000003213 activating effect Effects 0.000 description 12
239000013078 crystal Substances 0.000 description 10
238000011160 research Methods 0.000 description 9
CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 8
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
239000005977 Ethylene Substances 0.000 description 7
230000009102 absorption Effects 0.000 description 7
238000010521 absorption reaction Methods 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000011521 glass Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
241001024304 Mino Species 0.000 description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
229920002554 vinyl polymer Polymers 0.000 description 6
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000011236 particulate material Substances 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
239000012876 carrier material Substances 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
230000005012 migration Effects 0.000 description 4
238000013508 migration Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000008569 process Effects 0.000 description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical compound CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 description 3
206010034972 Photosensitivity reaction Diseases 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000000295 complement effect Effects 0.000 description 3
238000011161 development Methods 0.000 description 3
230000018109 developmental process Effects 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229960005419 nitrogen Drugs 0.000 description 3
230000036211 photosensitivity Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
125000002723 alicyclic group Chemical group 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000002301 combined effect Effects 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
239000000975 dye Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
230000006872 improvement Effects 0.000 description 2
239000011810 insulating material Substances 0.000 description 2
230000003993 interaction Effects 0.000 description 2
239000001282 iso-butane Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
238000003801 milling Methods 0.000 description 2
239000000178 monomer Substances 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
231100000489 sensitizer Toxicity 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
FUOSTELFLYZQCW-UHFFFAOYSA-N 1,2-oxazol-3-one Chemical class OC=1C=CON=1 FUOSTELFLYZQCW-UHFFFAOYSA-N 0.000 description 1
PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
PDBZHEMVWXFWIT-UHFFFAOYSA-N 1-[4-(n-phenylanilino)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 PDBZHEMVWXFWIT-UHFFFAOYSA-N 0.000 description 1
GZZLQUBMUXEOBE-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diol Chemical compound OCCC(C)CC(C)(C)CO GZZLQUBMUXEOBE-UHFFFAOYSA-N 0.000 description 1
PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
JZUMVFMLJGSMRF-UHFFFAOYSA-N 2-Methyladipic acid Chemical compound OC(=O)C(C)CCCC(O)=O JZUMVFMLJGSMRF-UHFFFAOYSA-N 0.000 description 1
WFUUAJVRMXKBBI-UHFFFAOYSA-N 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1(CCO)CCCCC1 WFUUAJVRMXKBBI-UHFFFAOYSA-N 0.000 description 1
LBTDHCQNAQRHCE-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)cyclohexyl]oxyethanol Chemical compound OCCOC1CCC(OCCO)CC1 LBTDHCQNAQRHCE-UHFFFAOYSA-N 0.000 description 1
LBZZJNPUANNABV-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)phenyl]ethanol Chemical compound OCCC1=CC=C(CCO)C=C1 LBZZJNPUANNABV-UHFFFAOYSA-N 0.000 description 1
OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
VNWZKNAMSKFTJA-UHFFFAOYSA-N 2-[n-ethyl-4-[1-[4-[ethyl(2-hydroxyethyl)amino]-2-methylphenyl]-2-methylpropyl]-3-methylanilino]ethanol Chemical compound CC1=CC(N(CCO)CC)=CC=C1C(C(C)C)C1=CC=C(N(CC)CCO)C=C1C VNWZKNAMSKFTJA-UHFFFAOYSA-N 0.000 description 1
CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 description 1
QPGBFKDHRXJSIK-UHFFFAOYSA-N 2-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=C(C(O)=O)C=CC=C1C(O)=O QPGBFKDHRXJSIK-UHFFFAOYSA-N 0.000 description 1
RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical class O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 description 1
WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
SQJQLYOMPSJVQS-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 SQJQLYOMPSJVQS-UHFFFAOYSA-N 0.000 description 1
BKZSPCUFQFNUIM-UHFFFAOYSA-N 4-[1-[4-(diethylamino)phenyl]-1-phenylethyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C)(C=1C=CC(=CC=1)N(CC)CC)C1=CC=CC=C1 BKZSPCUFQFNUIM-UHFFFAOYSA-N 0.000 description 1
KIGTXAWIOISJOG-UHFFFAOYSA-N 4-methoxy-n,n-diphenylaniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 KIGTXAWIOISJOG-UHFFFAOYSA-N 0.000 description 1
QGNQEODJYRGEJX-UHFFFAOYSA-N 4h-isoquinoline-1,3-dione Chemical class C1=CC=C2C(=O)NC(=O)CC2=C1 QGNQEODJYRGEJX-UHFFFAOYSA-N 0.000 description 1
PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241001561902 Chaetodon citrinellus Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
235000010676 Ocimum basilicum Nutrition 0.000 description 1
240000007926 Ocimum gratissimum Species 0.000 description 1
240000008881 Oenanthe javanica Species 0.000 description 1
101150050192 PIGM gene Proteins 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical class C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
230000032683 aging Effects 0.000 description 1
238000005882 aldol condensation reaction Methods 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
230000004075 alteration Effects 0.000 description 1
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
229910001864 baryta Inorganic materials 0.000 description 1
230000008901 benefit Effects 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
229910052729 chemical element Inorganic materials 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000004020 conductor Substances 0.000 description 1
FJENHLKDNJIZJE-UHFFFAOYSA-N cyclobutene Chemical compound C1C[C+]=C1 FJENHLKDNJIZJE-UHFFFAOYSA-N 0.000 description 1
XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical class OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
150000001934 cyclohexanes Chemical class 0.000 description 1
LNGJOYPCXLOTKL-UHFFFAOYSA-N cyclopentane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C1 LNGJOYPCXLOTKL-UHFFFAOYSA-N 0.000 description 1
FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
125000002644 dihydroxyphenylene group Chemical group OC1=C(C(=C(C=C1)*)*)O 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 1
YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
229910003437 indium oxide Inorganic materials 0.000 description 1
PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000011256 inorganic filler Substances 0.000 description 1
229910003475 inorganic filler Inorganic materials 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
125000005395 methacrylic acid group Chemical class 0.000 description 1
CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 1
238000005648 named reaction Methods 0.000 description 1
DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
JSKSILUXAHIKNP-UHFFFAOYSA-N naphthalene-1,7-dicarboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=CC(C(=O)O)=CC=C21 JSKSILUXAHIKNP-UHFFFAOYSA-N 0.000 description 1
RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012766 organic filler Substances 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229920002382 photo conductive polymer Polymers 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
NKWWLZYIEKKJHB-UHFFFAOYSA-N potassium;bis[(3-carboxyphenyl)sulfonyl]azanide Chemical compound [K+].OC(=O)C1=CC=CC(S(=O)(=O)[N-]S(=O)(=O)C=2C=C(C=CC=2)C(O)=O)=C1 NKWWLZYIEKKJHB-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
ADXCEOBGDCQCKM-UHFFFAOYSA-N quinoline-2,3-dione Chemical compound C1=CC=CC2=NC(=O)C(=O)C=C21 ADXCEOBGDCQCKM-UHFFFAOYSA-N 0.000 description 1
230000004044 response Effects 0.000 description 1
239000000523 sample Substances 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
JAQPLMRYRQJNNP-UHFFFAOYSA-N sodium;bis[(4-carboxyphenyl)sulfonyl]azanide Chemical compound [Na+].C1=CC(C(=O)O)=CC=C1S(=O)(=O)[N-]S(=O)(=O)C1=CC=C(C(O)=O)C=C1 JAQPLMRYRQJNNP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
PEQHIRFAKIASBK-UHFFFAOYSA-N tetraphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PEQHIRFAKIASBK-UHFFFAOYSA-N 0.000 description 1
IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
230000009974 thixotropic effect Effects 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000012780 transparent material Substances 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
238000006886 vinylation reaction Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G17/00—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process
- G03G17/04—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process using photoelectrophoresis
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Electrochemistry (AREA)
Molecular Biology (AREA)
Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Photoreceptors In Electrophotography (AREA)
Polyesters Or Polycarbonates (AREA)

CA000401503A 1981-04-22 1982-04-22 Polyesters ioniques pour particules produits et elements electriquement photosensibles, et methodes de formation photoelectrophoretique d'images Expired CA1182242A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/256,338 US4361636A (en)	1981-04-22	1981-04-22	Ionic polyesters for electrically photosensitive composite particles, materials, elements and photoelectrophotoretic imaging methods
US256,338		1988-10-11

Publications (1)

Publication Number	Publication Date
CA1182242A true CA1182242A (fr)	1985-02-05

Family

ID=22971873

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000401503A Expired CA1182242A (fr)	1981-04-22	1982-04-22	Polyesters ioniques pour particules produits et elements electriquement photosensibles, et methodes de formation photoelectrophoretique d'images

Country Status (5)

Country	Link
US (1)	US4361636A (fr)
EP (1)	EP0064007B1 (fr)
JP (1)	JPS57182319A (fr)
CA (1)	CA1182242A (fr)
DE (1)	DE3268631D1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4463078A (en) *	1981-07-20	1984-07-31	Eastman Kodak Company	Condensation polymeric photoconductors containing pendant arylamines
US4609606A (en) *	1985-04-01	1986-09-02	Eastman Kodak Company	Polyesters comprising recurring photoconductive and photocrosslinkable units and elements thereof
US4877699A (en) *	1988-08-25	1989-10-31	Eastman Kodak Company	Electrophotographic luminescent amplification process
JP2802518B2 (ja) *	1989-10-13	1998-09-24	戸田工業株式会社	磁気記録媒体
US5733695A (en) *	1995-11-27	1998-03-31	Eastman Kodak Company	Electrophotographic elements with generating layers containing polyester ionomers
KR100379442B1 (ko) *	2000-12-12	2003-04-11	엘지전자 주식회사	유기전계발광소자
WO2009048653A1 (fr) *	2007-05-18	2009-04-16	Polyfuel, Inc.	Polymères fonctionnalisés conducteurs d'ions à groupes bis(aryl)sulfonimides
WO2022167713A1 (fr) *	2021-02-04	2022-08-11	Kone Corporation	Élément d'ascenseur, son procédé de fabrication et ascenseur

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE755461A (fr) *	1969-08-29	1971-03-01	Bayer Ag	Polyesters contenant des atomes d'azote tertiaires
US3703372A (en) *	1971-11-04	1972-11-21	Eastman Kodak Co	Photoconductive elements containing polymeric binders
US3923509A (en) *	1973-05-21	1975-12-02	Ici America Inc	Water-soluble polyester resins as binders for photoconductors
US4284699A (en) *	1977-02-14	1981-08-18	Eastman Kodak Company	Polyester binder component in multilayer photoconductive element
US4322487A (en) *	1979-08-08	1982-03-30	Eastman Kodak Company	Composite electrically photosensitive particles for electrophoretic migration imaging process
US4252921A (en) *	1979-10-03	1981-02-24	Eastman Kodak Company	Polyesterionomers having utility in liquid electrographic developer compositions

1981
- 1981-04-22 US US06/256,338 patent/US4361636A/en not_active Expired - Fee Related
1982
- 1982-04-22 JP JP57068018A patent/JPS57182319A/ja active Pending
- 1982-04-22 CA CA000401503A patent/CA1182242A/fr not_active Expired
- 1982-04-22 DE DE8282400720T patent/DE3268631D1/de not_active Expired
- 1982-04-22 EP EP82400720A patent/EP0064007B1/fr not_active Expired

Also Published As

Publication number	Publication date
EP0064007A1 (fr)	1982-11-03
EP0064007B1 (fr)	1986-01-22
DE3268631D1 (en)	1986-03-06
US4361636A (en)	1982-11-30
JPS57182319A (en)	1982-11-10

Legal Events

Date	Code	Title	Description
2002-02-06	MKEC	Expiry (correction)
2002-04-22	MKEX	Expiry

Publication	Publication Date	Title
US3442781A (en)	1969-05-06	Photoelectrophoretic and xerographic imaging processes employing triphenodioxazines as the electrically photosensitive component
US4146707A (en)	1979-03-27	Heterocyclic ethenyl or vinyl heterocyclic or aromatic compounds for migration imaging processes
US4012376A (en)	1977-03-15	Photosensitive colorant materials
US4311775A (en)	1982-01-19	Novel phthalocyanine pigments and electrophotographic uses thereof
US4314013A (en)	1982-02-02	Particle formation by double encapsulation
EP0024169A2 (fr)	1981-02-25	Particules électrophotosensibles pour des procédés de formation d'images par migration électrophorétique, dispersions contenant ces particules et procédé utilisant de telles dispersions
US4175956A (en)	1979-11-27	Electrophotosensitive materials for migration imaging processes
CA1182242A (fr)	1985-02-05	Polyesters ioniques pour particules produits et elements electriquement photosensibles, et methodes de formation photoelectrophoretique d'images
US4135925A (en)	1979-01-23	Methods of changing color by image disruption
US4197120A (en)	1980-04-08	Electrophoretic migration imaging process
US4382033A (en)	1983-05-03	Novel phthalocyanine pigments
US3741760A (en)	1973-06-26	Imaging system
US3448029A (en)	1969-06-03	Electrophoretic imaging process using 8,13-dioxodinaphtho - (2,1 - b; 2',3'-d) - furan-6-carboxamide pigments
US4331751A (en)	1982-05-25	Electrically photosensitive materials and elements for photoelectrophoretic imaging processes
US4282354A (en)	1981-08-04	Electrophoretic migration imaging process
US4113482A (en)	1978-09-12	Migration imaging method involving color change
US3912505A (en)	1975-10-14	Color imaging method employing a monolayer of beads
US4142890A (en)	1979-03-06	Photosensitive trans-epindolidione pigment for migration imaging processes
US3857549A (en)	1974-12-31	Photoelectrophoretic imaging apparatus
US3676313A (en)	1972-07-11	Removing undesired potential from the blocking electrode in a photoelectrophoretic imaging system
US3448030A (en)	1969-06-03	Electrically photosensitive particles useful in photoelectrophoretic and xerographic imaging processes
US4258112A (en)	1981-03-24	Sensitizer for electrophoretic migration imaging dispersions
US4219614A (en)	1980-08-26	Electrophoretic migration imaging composition and process using same
US4165984A (en)	1979-08-28	Electrophoretic migration imaging process
US5356741A (en)	1994-10-18	Control of the acid/base environment in photoconductive elements